Naphthalene compounds

a technology of naphthalene and compounds, applied in the field of naphthalene compounds, can solve the problem of short half-life of naphthalene,

Inactive Publication Date: 2000-11-07
LES LAB SERVIER
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its half-life is, however, quite short owing to its being rapidly metabolised.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

N-[2-(7-Methoxy-3-trifluoromethanesulphonyloxy-1-naphthyl)ethyl]acetamide

Step a: N-[2-(3-Acetyl-7-methoxy-1-naphthyl)ethyl]acetamide

0.45 mol (60 g) of aluminium chloride are added at 0.degree. C. to a solution of 0.16 mol (40 g) of N-[2-(7-methoxy-1-naphthyl)ethyl]acetamide (described in Patent EP 447 285) in 350 ml of dichloromethane. 0.21 mol (15.3 ml) of acetyl chloride is then added dropwise at 0.degree. C. The reaction medium is stirred at room temperature for 1 hour and then poured onto ice. The organic phase is decanted and concentrated to yield the expected compound.

Step b: N-[2-(3-Hydroxy-7-methoxy-1-naphthyl)ethyl]acetamide.

0.32 mol (54 g) of meta-chloroperoxybenzoic acid is added to a suspension of 0.16 mol (46 g) of the compound described in the preceding Step in 1.4 litres of dichloromethane. The reaction medium is stirred at room temperature for 20 hours. The mixture is then washed with water, and the excess acid is extracted with a molar solution of sodium hydrogen ca...

example 2

N-[2-(7-Methoxy-3-phenyl-1-naphthyl)ethyl]acetamide

0.1 mol (13.3 g) of phenylboric acid, 1.8 g of palladium(0) tetrakistriphenylphosphine and 5.5 g of lithium chloride are added under an inert atmosphere to a solution of 0.067 mol (24.5 g) of the compound described in Example 1 in 225 ml of dimethoxyethane. The reaction mixture is stirred for 10 minutes and then 160 ml of a molar solution of sodium carbonate and 110 ml of absolute ethanol are added. The reaction mixture is heated at 90.degree. C. for 4 hours. After cooling, 500 ml of 1M sodium carbonate are added, and the reaction mixture is extracted twice with 500 ml of dichloromethane. The organic phase is dried, concentrated and purified by chromatography on silica gel, using ethyl acetate as eluant, to yield the expected compound.

Melting point: 135.degree. C.

example 3

N-[2-(7-Methoxy-3-phenyl-1-naphthyl)ethyl]propionamide

Step a: N-[2-(7-Methoxy-3-trifluoromethanesulphonyloxy-1-naphthyl)ethyl]propionamide

The expected product is obtained according to the process described in Example 1, Steps a and b, starting from N-[2-(7-methoxy-1-naphthyl)ethyl]propionamide described in Patent EP 447 285.

Step b: N-[2-(7-Methoxy-3-phenyl-1-naphthyl)ethyl]propionamide

The expected product is obtained according to the process described in Example 2 starting from the compound described in the preceding Step.

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Abstract

Compound of formula (I): wherein: T represents alkylene, A and B together form a naphthalene, dihydronaphthalene, or tetrahydronaphthalene group, R represents hydrogen, hydroxy, R' or OR', R' being as defined in the description, G1 represents halogen, a radical R1 or a group -O-CO-R1, R1 being as defined in the description, G2 represents a group selected from: X, R2 and R21 being as defined in the description, and medicinal products containing the same which are useful in the treatment of a condition related to the melatoninergic system.

Description

The present invention relates to new compounds having a naphthalene structure.DESCRIPTION OF THE PRIOR ARTPatent Specifications EP 447 285, EP 530 087 and EP 562 956 describe naphthylalkyl-amide, naphthylalkylurea and naphthylalkylthiourea compounds having valuable pharmacological properties by virtue of their affinity for melatonin receptors and their agonist or antagonist character. All those compounds are characterised by the presence of a single substituent on the ring structure carrying the alkylamide or alkylurea chain. Application WO 9706140 describes closely related melatoninergic ligands that are acylated on the main ring structure carrying the alkylamide chain.Many studies in the last ten years have shown the key role of melatonin (N-acetyl-5-methoxytryptamine) in many physiopathological phenomena and in the control of circadian rhythm. Its half-life is, however, quite short owing to its being rapidly metabolised. It is thus very valuable to be able to provide the clinicia...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C07C233/58C07C233/18C07C233/47C07C275/24C07C309/65C07C233/31C07C233/05C07C309/00C07C233/00C07C255/66C07C275/00C07C255/00C07C233/36C07C233/60C07D307/00C07D307/52C07D333/00C07D333/20A61K31/00A61K31/10A61K31/16A61K31/165A61K31/17A61K31/18A61K31/34A61K31/341A61K31/38A61K31/381A61K31/44A61K31/4402A61K31/4406A61P25/20A61P43/00C07C233/17C07C233/22C07C317/14C07C317/22C07C317/32C07C327/42C07C335/06C07D213/56C07D233/60C07D307/12C07D307/54C07D333/16
CPCC07D333/20C07C233/18C07C233/31C07C233/36C07C233/47C07C233/58C07C233/60C07C255/66C07C275/24C07C309/65C07D307/52C07C233/05C07B2200/07C07C2101/02C07C2101/04C07C2102/10C07C2601/02C07C2601/04C07C2602/10A61P25/20A61P43/00
Inventor LEFOULON, FRAN.CEDILLA.OISDEMUYNCK, LUCLESIEUR, DANIELDEPREUX, PATRICKBENNEJEAN, CAROLINERENARD, PIERREDELAGRANGE, PHILIPPE
Owner LES LAB SERVIER
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